GB1113578A - Method of producing tertiary phosphines - Google Patents
Method of producing tertiary phosphinesInfo
- Publication number
- GB1113578A GB1113578A GB4676166A GB4676166A GB1113578A GB 1113578 A GB1113578 A GB 1113578A GB 4676166 A GB4676166 A GB 4676166A GB 4676166 A GB4676166 A GB 4676166A GB 1113578 A GB1113578 A GB 1113578A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphine
- aqueous phase
- aqueous
- acid
- ammonia
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- 150000003003 phosphines Chemical group 0.000 title abstract 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 12
- 239000008346 aqueous phase Substances 0.000 abstract 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 6
- -1 phosphorus halide Chemical class 0.000 abstract 5
- 229910052698 phosphorus Inorganic materials 0.000 abstract 4
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 239000012074 organic phase Substances 0.000 abstract 3
- 239000011574 phosphorus Substances 0.000 abstract 3
- 239000011541 reaction mixture Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000011260 aqueous acid Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
- C07F9/5068—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure >P-Hal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Tertiary phosphines R1R2R3P are obtained by reacting in an organic solvent a Grignard compound RMgX with a phosphorus halide PX3, R1PX2 or R1R2PX, wherein R, R1, R2 and R3 which may be the same or different are straight or branched chain alkyl, alkenyl, alkinyl, aralkyl, cycloalkyl, aryl or substituted aryl radicals which radicals may optionally also contain interrupting hetero atoms, e.g. oxygen, and X is Cl, Br or I and which may be the same or different, n mols. of the Grignard compound being reacted per 0.8 to 1.1 mol. of the phosphorus halide where n is the number of halogen atoms in the phosphorus halide molecule bound to P, at a temperature of - 70 DEG to 80 DEG C., preferably -10 DEG to 30 DEG C., and the phosphine being isolated from the reaction mixture either by (1) adding only sufficient water for the water to combine with the resulting magnesium halide to form a granular adduct without forming an aqueous phase, or by (ii) adding water to form an aqueous phase, adding acid and then, after neutralization to a pH of at least 6.0 with a base, e.g. ammonia or a basic amine, separating the phosphine either from the organic phase or from the aqueous phase. The reaction and working up should normally be carried out under an inert gas such as nitrogen. Specified solvents for carrying out the reaction are diethyl-, diisopropyl- and dibutyl ethers, tetrahydrofuran, dioxane and aliphatic or aromatic hydrocarbons optionally mixed with an ether or other solvent. In one form of separation by method (ii) the reaction mixture is mixed suitably at -10 DEG to 50 DEG C. with an aqueous acid, e.g. aqueous HCl or NH4Cl, until all the magnesium halide has dissolved, e.g. at pH 1 to 6 and the mixture is then adjusted with a base, e.g. ammonia or a basic amine, to at least pH 6.0. After separation of the aqueous phase the phosphine is recovered from the organic phase by fractional distillation. If the phosphine is soluble in acid it can be isolated from the aqueous phase, thus aqueous acid is added to the reaction mixture to dissolve the phosphine in the aqueous phase, the aqueous and organic phases are separated and the pH of the aqueous phase is adjusted to at least 6.0, e.g. by adding ammonia, to precipitate the phosphine which is then separated.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED48468A DE1265746B (en) | 1965-10-21 | 1965-10-21 | Process for the production of tertiary phosphines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1113578A true GB1113578A (en) | 1968-05-15 |
Family
ID=7051195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4676166A Expired GB1113578A (en) | 1965-10-21 | 1966-10-19 | Method of producing tertiary phosphines |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE688558A (en) |
| CH (1) | CH485777A (en) |
| DE (1) | DE1265746B (en) |
| FR (1) | FR1504670A (en) |
| GB (1) | GB1113578A (en) |
| NL (1) | NL6614945A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105330691A (en) * | 2015-12-08 | 2016-02-17 | 山东维天精细化工科技有限公司 | Synthetic method for triethylphosphine |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1247310B (en) * | 1966-08-10 | 1967-08-17 | Basf Ag | Process for the production of tertiary phosphines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2912465A (en) * | 1956-07-23 | 1959-11-10 | Metal & Thermit Corp | Process for preparing organophosphines |
| US3048638A (en) * | 1958-09-04 | 1962-08-07 | Union Carbide Corp | Vinyl phosphines |
-
1965
- 1965-10-21 DE DED48468A patent/DE1265746B/en active Pending
-
1966
- 1966-10-14 CH CH1483466A patent/CH485777A/en not_active IP Right Cessation
- 1966-10-19 GB GB4676166A patent/GB1113578A/en not_active Expired
- 1966-10-20 FR FR80829A patent/FR1504670A/en not_active Expired
- 1966-10-20 BE BE688558D patent/BE688558A/xx unknown
- 1966-10-21 NL NL6614945A patent/NL6614945A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105330691A (en) * | 2015-12-08 | 2016-02-17 | 山东维天精细化工科技有限公司 | Synthetic method for triethylphosphine |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1504670A (en) | 1967-12-08 |
| DE1265746B (en) | 1968-04-11 |
| BE688558A (en) | 1967-03-31 |
| NL6614945A (en) | 1967-04-24 |
| CH485777A (en) | 1970-02-15 |
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